Biz Stone in 2009. The co-founder of Twitter hopes the best parts of a failed venture will mean success for his new business.
Photograph: Mike Kepka/The Chronicle

When Twitter co-founder Biz Stone’s new company started to wobble he turned to “bright spot theory” for an answer.

The 40-year-old multi-millionaire’s first post-Twitter foray, a Q&A app called Jelly, was struggling to attract users after its January launch. But the ever optimistic Stone saw an opportunity, one that last month became a quirky new image- and message-sharing app called Super.

Stone talks about “bright spot theory” in his book, Things a Little Bird Told Me. It’s a concept tailor-made for Silicon Valley. The basic idea is that when the clouds roll in, you look past the disappointments and identify at least one ray of sunshine, however small it might be. You then double down on that and ignore everything else.

That’s what Stone says he was ready to do a few months after launching Jelly. Originally envisioned as a way for people to tap social network users for answers to questions, it didn’t catch on the way Stone & Co had hoped. So the team holed themselves up at the Cavallo Point lodge in San Francisco to search for a solution.

“When we launched Jelly, it was kind of my first thing since Twitter, and it zoomed to 1m downloads in like 48 hours,” Stone said. “It had taken us two and a half years to get to 1m downloads for Twitter, so it was like – oh my God, this thing is crazy. And then three months in, things weren’t looking right.

“The biggest problem was that people either didn’t want to ask a question or didn’t have a question to ask. When they did have questions, it worked like a charm. The problem was we didn’t have enough people asking questions. I figured we had enough money in the bank and talent to work on Jelly for the next four or five years. But even though my hallucinogenic optimism told me all people want to do is help each other, my hunch was that Jelly probably wouldn’t be the next big search engine.”

It was an insight that shifted Stone’s ambitions down a different path. Rather than launch another product that depended on gathering as many users as possible from the get-go, Jelly would change course. The new focus: build something new that was just fun instead, and worry about the rest later. Stone said he was thinking at least in part about Twitter’s early days, when the founders first cobbled together a social playground with seemingly few rules and then turned users loose on it, watching the behavior patterns that followed.

There was no master plan for Twitter at the start, he points out. The plan, and the service’s identity, evolved over time.

“If you build something fun, people are more likely to use it,” Stone said. “And if a lot of people use it, then it has the potential to be important.”

Figuring out what his company’s new fun thing would be started with Stone quizzing Jelly COO Kevin Thau over what the numbers were saying about Jelly. Thau told him, basically, it was a flop.

“I asked him to tell me what was good, and he said the usage was flat, we’re screwed and everything sucks,” Stone recalls. “I said, ‘Really? C’mon, let’s look at it together. And we found something interesting going on. For the questions that were being asked, the ratio (of questions to answers) was bonkers. One question could get like 30 answers. It was clear some people really love answering questions. I said, ‘Kevin, people seem to like to publish their opinion online.’”

So the team locked themselves in a room and decided not to leave until they had a pitch for a new product to build. Ideas were bandied about on variations of Jelly’s question-and-answer model, while Stone instead decided the question piece of the puzzle was just getting in the way for most people.

He sketched an iPhone that displayed an image of the Golden Gate Bridge, over which was written the number of rivets that are part of the bridge and included a simple declaration that “it’s awesome!” How about something like this? Stone suggested. What if we give people a way to share images and write text on top of them in a stylized way, as an outlet through which to creatively express themselves?

Talk then turned to what kind of constraints to employ, and the Jelly team came up with the idea that users could express any opinion, but they had to do so using phrases the app would start them off with. Phrases like “The Best,” “I Love” or “Current Status.” The “starters” tended to be superlatives, someone pointed out. So they decided to name the app Super.

“And why wouldn’t you want to download something called Super?” Stone continued. “It took two weeks to hack together something that worked. And then once we were using it, we were just giggling and laughing and stuff. It’s like when we started Twitter, we were totally just goofing around. Anything other than that is revisionist history. Snapchat is the same – it’s this silly, fun thing but has become an important communications tool. Facebook started with people hooking up in dorms, and now it’s one of the most important companies in the world. We said, let’s let everyone be a little pop artist. I started out as an artist, and now we’re making this fun thing that lets people create bits of art that are expressive and fun. That’s really all it is. I’m not trying to say this is disruptive. It’s just like graphic design, which mashes up existing things to create something new.”

Already, users of Super range from L’Oreal to high school students in Florida. The goofy-looking posts are heavy on design, true to Stone’s roots. He said the app’s aesthetic was inspired by his fascination with American pop artist Barbara Kruger, who layers collages of words over striking images. Whether Super can find a following remains to be seen. Stone’s old Twitter pals Ev Williams and Jack Dorsey have both gone on to found interesting new businesses. Medium, Williams’s writing platform, now has 17 million visitors a month; President Barack Obama has been among its high-profile writers. Square, Dorsey’s online payments system, is duking it out in the competitive, and potentially very rewarding, world of mobile money. Stone’s pitch is more whimsical.

“The same motivation has always been true for me, which is you want to build things, and you want to leave something behind and all that jazz,” Stone said. “I never really stopped being an artist. It occurred to me a few years ago that although I don’t paint as much as I used to, I now create these systems so other people can be artists. So it’s like, that’s my art. My art is these elaborate, self-organizing tools of communication that enable people to become artists themselves.”